Electrochemical reactions. Part II. The structure of an unusual product from the reduction of 1-acetylnaphthalene

Abstract

Electro-reduction of 1-acetylnaphthalene in alkaline solution gave the substituted tetrahydro-1,4-methano-3-benzoxepin (I) and not the expected pinacol. The structure of this compound is deduced from its spectral properties and its conversion into 1-(4-acetyl-1-naphthyl)-1-(1-naphthyl)ethane (II) on treatment with acid. The reduction of 1-acetylnaphthalene in neutral medium also gave (I). In acid medium 1-ethylnaphthalene and an organomercury compound were formed.